JP2000510852A - スルホニル―メルカプト―トリアゾリル誘導体およびそれらの殺微生物剤としての使用 - Google Patents
スルホニル―メルカプト―トリアゾリル誘導体およびそれらの殺微生物剤としての使用Info
- Publication number
- JP2000510852A JP2000510852A JP09541473A JP54147397A JP2000510852A JP 2000510852 A JP2000510852 A JP 2000510852A JP 09541473 A JP09541473 A JP 09541473A JP 54147397 A JP54147397 A JP 54147397A JP 2000510852 A JP2000510852 A JP 2000510852A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- halogen
- alkyl
- atoms
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000003641 microbiacidal effect Effects 0.000 title claims abstract description 10
- 229940124561 microbicide Drugs 0.000 title claims abstract description 5
- -1 Sulfonyl-mercapto-triazolyl Chemical class 0.000 title claims description 184
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 168
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 35
- 229910052751 metal Chemical class 0.000 claims abstract description 22
- 239000002184 metal Chemical class 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 437
- 125000005843 halogen group Chemical group 0.000 claims description 116
- 229910052736 halogen Inorganic materials 0.000 claims description 104
- 150000002367 halogens Chemical class 0.000 claims description 95
- 125000001424 substituent group Chemical group 0.000 claims description 84
- 239000000460 chlorine Substances 0.000 claims description 82
- 229910052801 chlorine Inorganic materials 0.000 claims description 81
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 73
- 229910052794 bromium Inorganic materials 0.000 claims description 73
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 125000001188 haloalkyl group Chemical group 0.000 claims description 43
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 37
- 125000004414 alkyl thio group Chemical group 0.000 claims description 25
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000004067 bulking agent Substances 0.000 claims 1
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 24
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 description 86
- 239000011737 fluorine Substances 0.000 description 85
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 78
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 56
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- 239000013543 active substance Substances 0.000 description 26
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 22
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 22
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 19
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 19
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
- 125000004429 atom Chemical group 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 235000019270 ammonium chloride Nutrition 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000012141 concentrate Substances 0.000 description 14
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 125000001153 fluoro group Chemical group F* 0.000 description 13
- 230000014509 gene expression Effects 0.000 description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 241000894007 species Species 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 230000001681 protective effect Effects 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 11
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 11
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 125000006426 1-chlorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(Cl)* 0.000 description 6
- 241000221787 Erysiphe Species 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- 239000012770 industrial material Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 150000003852 triazoles Chemical class 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- 241001465180 Botrytis Species 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 125000005429 oxyalkyl group Chemical group 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 241000221198 Basidiomycota Species 0.000 description 3
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000682843 Pseudocercosporella Species 0.000 description 3
- 241000589516 Pseudomonas Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- BQMRHYBXRAYYQS-UHFFFAOYSA-N 4-dihydroxyphosphinothioyloxy-n,n-diethyl-6-methylpyrimidin-2-amine Chemical compound CCN(CC)C1=NC(C)=CC(OP(O)(O)=S)=N1 BQMRHYBXRAYYQS-UHFFFAOYSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- 241000223600 Alternaria Species 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000223651 Aureobasidium Species 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001600093 Coniophora Species 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 2
- 239000005947 Dimethoate Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000005780 Fluazinam Substances 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
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- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19620590A DE19620590A1 (de) | 1996-05-22 | 1996-05-22 | Sulfonyl-mercapto-triazolyl-Derivate |
| DE19620590.5 | 1996-05-22 | ||
| PCT/EP1997/002408 WO1997044332A1 (de) | 1996-05-22 | 1997-05-12 | Sulfonyl-mercapto-triazolyl-derivate und ihre verwendung als mikrobizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000510852A true JP2000510852A (ja) | 2000-08-22 |
Family
ID=7795004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09541473A Pending JP2000510852A (ja) | 1996-05-22 | 1997-05-12 | スルホニル―メルカプト―トリアゾリル誘導体およびそれらの殺微生物剤としての使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6080775A (es) |
| EP (1) | EP0901477B1 (es) |
| JP (1) | JP2000510852A (es) |
| CN (1) | CN1226238A (es) |
| AU (1) | AU2896597A (es) |
| BR (1) | BR9709258A (es) |
| DE (2) | DE19620590A1 (es) |
| ES (1) | ES2207732T3 (es) |
| WO (1) | WO1997044332A1 (es) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006502994A (ja) * | 2002-07-22 | 2006-01-26 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ２−［２−（１−クロロシクロプロピル）−３−（２−クロロフェニル）−２−ヒドロキシプロピル］−２，４−ジヒドロ−３ｈ−１，２，４−トリアゾール−３−チオンの結晶変態ｉｉ型 |
| JP2011506539A (ja) * | 2007-12-19 | 2011-03-03 | ビーエーエスエフ ソシエタス・ヨーロピア | アゾリルメチルオキシラン類、それらの使用及びそれらを含む組成物 |
| JP2011506543A (ja) * | 2007-12-19 | 2011-03-03 | ビーエーエスエフ ソシエタス・ヨーロピア | アゾリルメチルオキシラン、その使用及びそれを含む薬剤 |
| JP2011507815A (ja) * | 2007-12-19 | 2011-03-10 | ビーエーエスエフ ソシエタス・ヨーロピア | アゾリルメチルオキシラン類、それらの使用およびそれらを含む組成物 |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19744706A1 (de) * | 1997-10-10 | 1999-04-15 | Bayer Ag | Verfahren zur Herstellung von Triazolinthion-Derivaten |
| WO2005090320A2 (en) * | 2004-03-12 | 2005-09-29 | Wyeth | Triazole derivatives and method of using the same to treat hiv infections |
| JP2012505156A (ja) * | 2008-10-07 | 2012-03-01 | ビーエーエスエフ ソシエタス・ヨーロピア | トリアゾールおよびイミダゾール化合物、その使用ならびにそれらを含む薬剤 |
| WO2010040718A1 (de) * | 2008-10-07 | 2010-04-15 | Basf Se | Triazol- und imidazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| WO2010122169A1 (en) * | 2009-04-24 | 2010-10-28 | Basf Se | 5-mercapto- [1,2, 4] triazole compounds and their agricultural and pharmaceutical uses |
| WO2010122170A1 (en) * | 2009-04-24 | 2010-10-28 | Basf Se | 5-mercapto- [1,2,4] triazolylmethyl-cyclopentanol compounds and their agricultural and pharmaceuti al uses |
| WO2010122167A1 (en) * | 2009-04-24 | 2010-10-28 | Basf Se | 5 -mercapto- [1, 2, 4] triazolylmethyl-cyclopentanol compounds and their agricultural and pharmaceutical uses |
| TW201041514A (en) * | 2009-04-24 | 2010-12-01 | Basf Se | Triazole compounds carrying a sulfur substituent II |
| BRPI1009073A2 (pt) | 2009-06-12 | 2016-03-01 | Basf Se | compostos de triazol das fórmulas i e ii, compostos das fórmulas i e ii, composição agrícola, uso de um composto da fórmula i ou ii, método para controlar fungos nocivos, semente, composição farmacêutica, uso de um composto da fórmula i ou ii e método para tratar câncer ou infecções por vírus ou para combater fungos patogênicos para seres humanos e para animais |
| EA201200020A1 (ru) | 2009-06-18 | 2012-07-30 | Басф Се | Фунгицидные смеси |
| CN102803231A (zh) | 2009-06-18 | 2012-11-28 | 巴斯夫欧洲公司 | 杀真菌的1，2，4-三唑衍生物 |
| BRPI1010096A2 (pt) | 2009-06-18 | 2016-03-15 | Basf Se | compostos de formulas i e ii, composição agrícola, uso de um composto, método de controle de fungos nocivos, semente, composição farmacêutica, uso de um composto e método de tratamento contra o câncer ou infecções por vírus ou para combater a fungos zoopatogênicos ou humanopatogênicos |
| WO2010146115A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
| EP2443097A1 (en) | 2009-06-18 | 2012-04-25 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
| CA2762512A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
| WO2010146116A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
| WO2010149758A1 (en) | 2009-06-25 | 2010-12-29 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
| BR112012001001A2 (pt) | 2009-07-14 | 2016-11-16 | Basf Se | compositos azol das formulas i e ii, compostos das formulas i e i, compostos de formula ix, composição agricola, uso de um composto farmaceutica, metodo para tratar infecções de câncer ou virus para combater fungos zoopatigênicos ou humanopatogenicos |
| WO2011069912A1 (de) | 2009-12-07 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| WO2011069894A1 (de) | 2009-12-08 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| WO2011069916A1 (de) | 2009-12-08 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung als fungizide sowie sie enthaltende mittel |
| JP2013514299A (ja) | 2009-12-18 | 2013-04-25 | ビーエーエスエフ ソシエタス・ヨーロピア | トリアゾリンチオン誘導体及びその中間体の製造方法 |
| US8729272B2 (en) | 2010-03-16 | 2014-05-20 | Basf Se | Process using grignard reagents |
| CN103228650A (zh) | 2010-09-30 | 2013-07-31 | 巴斯夫欧洲公司 | 合成含有硫代三唑并基团的化合物的方法 |
| CN106674138B (zh) * | 2016-11-21 | 2018-11-27 | 河南科技大学 | 一种戊唑醇新型半抗原及其合成方法和应用 |
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| US4048318A (en) * | 1972-01-11 | 1977-09-13 | Bayer Aktiengesellschaft | 1-Substituted-1,2,4-triazole fungicides |
| US3912752A (en) * | 1972-01-11 | 1975-10-14 | Bayer Ag | 1-Substituted-1,2,4-triazoles |
| US4147791A (en) * | 1972-01-11 | 1979-04-03 | Bayer Aktiengesellschaft | 1-Substituted-1,2,4-triazole fungicidal compositions and methods for combatting fungi that infect or attack plants |
| DE2324010C3 (de) * | 1973-05-12 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen |
| US4079062A (en) * | 1974-11-18 | 1978-03-14 | Janssen Pharmaceutica N.V. | Triazole derivatives |
| ZA774497B (en) * | 1976-07-29 | 1978-06-28 | Ici Ltd | Processes and compositions for combating fungi |
| IE45765B1 (en) * | 1976-08-19 | 1982-11-17 | Ici Ltd | Triazoles and imidazoles useful as plant fungicides and growth regulating agents |
| US4598085A (en) * | 1977-04-27 | 1986-07-01 | Janssen Pharmaceutica N.V. | Fungicidal 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles |
| US4654332A (en) * | 1979-03-07 | 1987-03-31 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| AU542623B2 (en) * | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
| GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
| AR228764A1 (es) * | 1980-12-20 | 1983-04-15 | Bayer Ag | 1-azolil-3,3-dimetilalcan(c3-4)-2-onas y-2-oles,sustituidos,procedimiento para su produccion y composiciones protectoras de plantas fungicidas y reguladoras del crecimiento de las plantas a base de dichos compuestos |
| DE3279417D1 (en) * | 1981-03-18 | 1989-03-09 | Ici Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| US5266585A (en) * | 1981-05-12 | 1993-11-30 | Ciba-Geigy Corporation | Arylphenyl ether derivatives, compositions containing these compounds and use thereof |
| DE3262386D1 (en) * | 1981-06-06 | 1985-03-28 | Pfizer Ltd | Antifungal agents, processes for their preparation, and pharmaceutical compositions containing them |
| DE3218130A1 (de) * | 1982-05-14 | 1983-11-17 | Basf Ag, 6700 Ludwigshafen | Azolylmethyloxirane, verfahren zu ihrer herstellung und diese enthaltende fungizide |
| CA1227801A (en) * | 1983-11-10 | 1987-10-06 | Ted T. Fujimoto | .alpha.-ALKYL-.alpha.-(4-HALOPHENYL)-1H-1,2,4-TRIAZOLE-1- PROPANENITRILES |
| CA1271764A (en) * | 1985-03-29 | 1990-07-17 | Stefan Karbach | Azolylmethyloxiranes, their preparation and their use as crop protection agents |
| DE3511411A1 (de) * | 1985-03-29 | 1986-10-02 | Basf Ag, 6700 Ludwigshafen | Verwendung von azolylmethyloxiranen zur bekaempfung von viralen erkrankungen |
| IT1204773B (it) * | 1986-01-23 | 1989-03-10 | Montedison Spa | Azolilderivati fungicidi |
| US4729986A (en) * | 1986-04-24 | 1988-03-08 | E. I. Du Pont De Nemours And Company | Fungicidal triazoles and imidazoles |
| US5084465A (en) * | 1986-06-23 | 1992-01-28 | Du Pont Merck Pharmaceutical Company | Antifungal carbinols |
| US4952232A (en) * | 1987-04-29 | 1990-08-28 | E. I. Du Pont De Nemours And Company | Antifungal carbinols |
| US4965281A (en) * | 1986-06-23 | 1990-10-23 | E. I. Du Pont De Nemours And Cmopany | Antifungal carbinols |
| EP0251086B1 (en) * | 1986-06-23 | 1993-03-17 | The Du Pont Merck Pharmaceutical Company | Antifungal carbinols |
| US5087635A (en) * | 1986-07-02 | 1992-02-11 | Rohm And Haas Company | Alpha-aryl-alpha-phenylethyl-1H-1,2,4-triazole-1-propanenitriles |
| JPH0625140B2 (ja) * | 1986-11-10 | 1994-04-06 | 呉羽化学工業株式会社 | 新規アゾール誘導体、その製造方法及び該誘導体の農園芸用薬剤 |
| DE3812967A1 (de) * | 1987-06-24 | 1989-01-05 | Bayer Ag | Azolylmethyl-cyclopropyl-derivate |
| DE3725397A1 (de) * | 1987-07-31 | 1989-02-09 | Bayer Ag | 1,4-disubstituierte 1-azolyl-3,3-dimethylbutan-derivate |
| US5256683A (en) * | 1988-12-29 | 1993-10-26 | Rhone-Poulenc Agrochimie | Fungicidal compositions containing (benzylidene)-azolylmethylcycloalkane |
| CA2006309C (fr) * | 1988-12-29 | 2001-12-18 | Jean Hutt | Azolylmethylcyclopentane benzylidene fongicide |
| US5308743A (en) * | 1989-06-29 | 1994-05-03 | Fuji Photo Film Co., Ltd. | Positive image-forming process utilizing glass substrate with oxide film of indium-tin alloy, coated with o-quinonediazide photoresist, with etching of the oxide film in the imagewise exposed areas |
-
1996
- 1996-05-22 DE DE19620590A patent/DE19620590A1/de not_active Withdrawn
-
1997
- 1997-05-12 CN CN97196668A patent/CN1226238A/zh active Pending
- 1997-05-12 US US09/194,508 patent/US6080775A/en not_active Expired - Fee Related
- 1997-05-12 ES ES97923054T patent/ES2207732T3/es not_active Expired - Lifetime
- 1997-05-12 JP JP09541473A patent/JP2000510852A/ja active Pending
- 1997-05-12 EP EP97923054A patent/EP0901477B1/de not_active Expired - Lifetime
- 1997-05-12 DE DE59710579T patent/DE59710579D1/de not_active Expired - Fee Related
- 1997-05-12 BR BR9709258A patent/BR9709258A/pt not_active IP Right Cessation
- 1997-05-12 WO PCT/EP1997/002408 patent/WO1997044332A1/de active IP Right Grant
- 1997-05-12 AU AU28965/97A patent/AU2896597A/en not_active Abandoned
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006502994A (ja) * | 2002-07-22 | 2006-01-26 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ２−［２−（１−クロロシクロプロピル）−３−（２−クロロフェニル）−２−ヒドロキシプロピル］−２，４−ジヒドロ−３ｈ−１，２，４−トリアゾール−３−チオンの結晶変態ｉｉ型 |
| JP4757490B2 (ja) * | 2002-07-22 | 2011-08-24 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ２−［２−（１−クロロシクロプロピル）−３−（２−クロロフェニル）−２−ヒドロキシプロピル］−２，４−ジヒドロ−３ｈ−１，２，４−トリアゾール−３−チオンの結晶変態ｉｉ型 |
| JP2011506539A (ja) * | 2007-12-19 | 2011-03-03 | ビーエーエスエフ ソシエタス・ヨーロピア | アゾリルメチルオキシラン類、それらの使用及びそれらを含む組成物 |
| JP2011506543A (ja) * | 2007-12-19 | 2011-03-03 | ビーエーエスエフ ソシエタス・ヨーロピア | アゾリルメチルオキシラン、その使用及びそれを含む薬剤 |
| JP2011507815A (ja) * | 2007-12-19 | 2011-03-10 | ビーエーエスエフ ソシエタス・ヨーロピア | アゾリルメチルオキシラン類、それらの使用およびそれらを含む組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0901477B1 (de) | 2003-08-13 |
| US6080775A (en) | 2000-06-27 |
| AU2896597A (en) | 1997-12-09 |
| BR9709258A (pt) | 1999-08-10 |
| CN1226238A (zh) | 1999-08-18 |
| WO1997044332A1 (de) | 1997-11-27 |
| DE19620590A1 (de) | 1997-11-27 |
| DE59710579D1 (de) | 2003-09-18 |
| EP0901477A1 (de) | 1999-03-17 |
| ES2207732T3 (es) | 2004-06-01 |
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